Reacción #81609

Ecuación de reacción

ethyl 3-[2-(t-butoxycarbonylamino)ethyl]-5-[(4-fluorophenyl)methyl]benzene-propanoate

trifluoracetic acid

→

title compound

Rendimiento 62.4%

Ethyl 3-(2-aminoethyl)-5-[(4-fluorophenyl)methyl]-benzenepropanoate

Rendimiento 62.4%

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroevaporated
2. 2
   OtroThe residue was partitioned between ether and dilute sodium hydroxide solution
3. 3
   OtroThe organic layer was separated
4. 4
   Lavadowashed with water
5. 5
   Secadodried (MgSO4)
6. 6
   OtroThe solvent was evaporated
7. 7
   Otrothe residue chromatographed on silica eluting with mixtures of dichloromethane, methanol and concentrated ammonium hydroxide
8. 8
   workup.ADDITIONThe product containing fractions
9. 9
   Otrothe solvent evaporated

Procedimiento

A solution of ethyl 3-[2-(t-butoxycarbonylamino)ethyl]-5-[(4-fluorophenyl)methyl]benzene-propanoate (2.36 g) and trifluoracetic acid (5 ml) in dichloromethane (25 ml) was allowed to stand at room temperature overnight and then evaporated. The residue was partitioned between ether and dilute sodium hydroxide solution. The organic layer was separated, washed with water and dried (MgSO4). The solvent was evaporated and the residue chromatographed on silica eluting with mixtures of dichloromethane, methanol and concentrated ammonium hydroxide. The product containing fractions were combined and the solvent evaporated to give the title compound as a gum (1.13 g), Rf 0.1 (SS 4). N.M.R. δ(CDCl3): 1.24 (3H,t), 1.48(2H,s), 2.61(2H,t), 2.73(2H,t), 2.90-2.98(4H,m), 3.93(2H,s), 4.14(2H,q), 6.88(2H,s), 6.91(1H,s), 6.96-7.03(2H,m), 7.12-7.18(2H,m).

Fuente